Method of producing new organic arsenic compounds



Patented Nova 6, 1923.

UNITED STATES PATENT OFFICE.

AUGUST ALBERT, OF MUNICH, GERMANY. ASSIGNOR TO TEE ROESSLER & HASS- LACHER CHEMICAL COMPANY, OF NEW YORK,

YORK.

N. Y., A CORPORATION 01 NEW METHOD OF PRODUCING NEW ORGANIC ARSENIC COMPOUNDS.

No Drawing.

To all whom it may concern:

Be it known that I, Ancus'r ALUERT, a citizen of the Republic of Genuany, and re siding at Munich, Elisabethstrssse 46, have invented certain new and useful Methods of Producing New Organic Arsenic Compounds, of which the following is a speci- -fication.

It is well known thatlhe arsenic acid group can be introduced into aromatic com pounds b diazotizing but only in those compoun s where there is no risk of interaction between the aromatic compound and the arsenic acid which has a strong reducing eflect.

I have discovered that by diezotizing arsenic can be introduced also into compounds containing the carbonyl group in spite of this group being easil acted u on by any reducing agent or in uence. he arsenic group-may therefore be introduced into aromatic or mixed aliphatic-aromatic aldehydos or ketones without the carbonyl group being affected thereby.

The technical importance of this experimental observation consists in the possibility of introducing arsenic into aromatic or mixed aliphatic-aromatic aldehydes or ketones or any substituted derivatives. Thus arsenic compounds are obtained capable of widely varied applications. The constitution of this class of compounds is shown by the following general formula:

one handeitheran unsubstituted aliphatic or aromatic or hydroaromatic radical, or on the other hand an aliphatic, aromatic .or

hydroaromatic radical substituted in any way for instance by a halogen, OH,

COOH, etc., further by a cyclic radical),

by R any c clic (carbocyclic or hetero cyclic) radica substituted or unsubstituted. The process can be carried out for example liy starting from a ketoneR LCOB NH s is diazotized and heated afterwards in presence of an arsenious salt-without taking any special recaution The reactiim ma take alkaline or acid so ution.

" E mfl vl- Nitrohydroxy acetylainido -noetophi1one place in neutral,

Application filcdlcbrusry 26, 1828. Serial Rn. 621,68.

Emampid 9.

2.7 g. g amid oaoetopherione are diazotiized with so 1am nitrite and jliydrochloric acid. After being made alkaline a solution of sodium arsenite is added. Here too the action is finished by heatin on a water bath The solution is acidifie by means of hydroa chloric acid, filtered and the clear solution concentrated after making it slight-1v alkaline in vacuo. 4 On addin hydrochloric acid the ketone-arsenious acid separates in needles FP 176?.

Ema'mple 3. I

2:7 g. aminobenzophenone hydrochloride are dissolved in about cc. water and .3 cc. hydrochloric acid (119) and diazol tized with 0.75 g. sodium nitrite in 4 cc.

water in the usnal'way. On adding 30 cc. n-NaOH solution and'LQO cc. of a solution containing sodium nrsenite .5) at once a strong evolution of nitrogen is noticed. By heating thdreaction is fin shed. hen after filtration the clear solution is acidified with hydrochloric acid, the benzophenonemonoarsoniousacid separates in crystals melting i In the same way the corresponding benzo henonediarsenious acid is Qbtliined from diamido-benzophenone (formed by .nitratmg amino benzophenone {and reducimg the derivative).- The acid may be crystallized V frot'tij'water and melts at 260. r

. i Ewa mple 5. 3.6 p-amidoi bonzaldehyde are diazotized in the ordinary way with sodium nitrite and hydrochloric acid. The diluted solution is then made alkaline wit-h soda lve. On Rding a solution of sodium arsenite large evolution of nitrogen sets in. The reaction is finished by heating on :t water-both. After adding an execs-s of hydrochloric acid the sediment. is filtered oil and the solution evaporated to dryness in vacuo. From the re idue the arsenious zit-id is extracted by means of alcohol. After evaporation the often oily residue stirred with a little water. The pm1tlehyrlwphony] arsenions arid (-rystallizes out. in needles.

The preseneeof the earhnnyl group is shown by the reaction with ihen 'thydrazin, the uh -nyl-hydt-nzonv there v being formed.

flint I claim is:

1. Method of producing new organic. arsenic compounds consistign in diazotizing mixed aliphatic-aromatic r-omponnds (ontaining reactive amino and onrhonvl groups and treating the resulting lJfltlV T l; m arsenite. I

2. Method of produ ing new o nnit :H- senie compounds eoni iting in dia'notizin; aromatic mom or tll \2tllll(ll ((l mmpounds. containinq reactive carbonyl groups and treating the r sulting hody with no arwnite.

In testimony whereof I have eignw! my name to this sperificution in the presence of two subscribing witnessw.

AUGUST A Llll-Ilt'l.

Witnesses:

VALnx'rrxr. WEICREL, C. C. L. B. Wrnss.

Certificate of Correction.

It is hereby certified that, in Letters Patent. No. 1,472,778, ranted November 6, 1923, upon We upplicntiun of August Albert, of Munich, elmany, for an imprnvement in Methmls of Producing Now Organic Arsenic Compounds, an error appears in the print9d spk'rifivation requiring correction as follows: Page 1, line 35, strike out the fflrmula and il'iSl'll insteudand that the said lmttvrs lntunl should lam-road with this correvtiun therein that the same may vnnfm'm m the revm-(l of the case in the Patent (Mice. Signed and swab-l (his 22;] day uf January, 1)., 1924.

[sun] FENNING,

' Acting Commissimer of Patents. 

